I watched in my side mirror as Constable K. Mueller returned to her squad car.
I had finished the “Walk a Mile in Her Shoes” march. It was a parade, not a race but my girlfriend Cheryl insisted that I best her nemesis Lori’s boyfriend Paul to the finish. Paul wore low heeled Mary Janes compared to my peep toed, five inch heeled stilettos so the results weren’t even close. Rather than going back to the office or driving directly home, Cheryl wanted to drink. There was no way she was in any shape to drive so I did in my high heels which turned out not to be the best idea.
Walking in the pointed heels was tough enough; having never driven with them on was a new experience. Modulating the gas and brakes while trying to steer led I guess led to some inconsistent manoeuvering. We were pulled over. When I couldn’t produce my driver’s licence, Constable Mueller had me step out of the car. That’s when she noticed my pretty, red shoes.
I explained why I was wearing them and that I had to drive since Cheryl was inebriated. Constable Mueller frisked me and of course could feel the straps of my garters holding up my stockings through the thin material of my summer pants.
In the end, she let us go. I managed to get home safely. Cheryl had recovered enough that she needed only slight support to help her in. Good thing, since walking in these shoes by myself was difficult enough.
Just as I opened the door, Cheryl spasmed a heaved. The tell-tale sign of tummy content rejection. She ran to the bathroom just in time to vomit. I followed her and aided in whatever way I could.
“Oh fuck! I feel like shit!” Cheryl spat out the water she used to rinse her mouth. “Thanks for getting me home, Sunshine. I hope everything was okay.”
I told her about being pulled over and not having my driver’s license with me. We returned to the living room. I got her some water to help rehydrate her. Cheryl smiled at my helpfulness and then noted. “You’re still wearing your shoes!”
I was so worried about my girlfriend that I absolutely forgot I had them on.
“Ping!” Cheryl’s phone sounded notifying her she had a new email.
“Fuck!” Cheryl spat out, this time in anger.”
“What it is?” I asked.
“The results of the fund raising for the march.” Cheryl looked very unhappy. “We were top ten in collections, but…”
I waited, then inquired. “But what?”
“We collected three thousand – two hundred – fifty dollars. Lori collected…” Cheryl started to tear. “… Three thousand – two hundred and sixty five.”
“Why are you crying? We did well. So what if she collected what? Fifteen dollars more? It’s great for the cause, isn’t it?” I tried to assure her.
“I’m sorry, Sunshine.” Tears ran down Cheryl’s cheek. “I made a bet with that bitch Lori. First that you would beat her wiener boyfriend to the finish and that I’d collect more money than she would.”
“It’s okay. What was the bet for?”
“Loser would have to clean the winner’s house.” Cheryl revealed.
“How bad can that be?”
“I’ve been to her place. It’s pretty big and…” Cheryl added. “You have to play maid.”
“What do you mean ‘maid’?” I asked.
“I was so sure we’d beat them during the march that I agreed to the bet.” Cheryl’ tears abated slightly. “Then she added the loser would have to also dress up for the part.”
Before I could ask about anything else, Cheryl’s mobile rang.
“Shit! It’s Lori! Didn’t take that bitch long.” Cheryl said looking at the caller ID. She swiped the green icon. “Hello, Lori… Yes, I got the email with the collections results… Yes, I know you collected more, but it was only fifteen dollars!”
There was a pause. I could hear muffled screaming coming from Cheryl’s phone as she held it far from her ear. Her eyes winced in pain from the loudness.
“Yes, I know a bet is a bet.” Cheryl said after the screaming stopped. “Okay. Good-b…”
“Bitch hung up in my ear!” Cheryl growled.
“Ping!” A message notification on Cheryl’s phone.
“You’ve got to be fucking kidding!” Cheryl said in awe.
“What is it?” I asked.
“That bitch sent me a picture of what she wants you to dress up in.” Cheryl held out her phone for me to look at. I took the phone from her and looked at the pic. Of course it was a stereo-typical French maid’s outfit: short frilly skirt with a white pinafore, black fishnet stockings and high heeled slut shoes.
My mouth was agape not believing what I was looking at.
“I am so sorry, Sunshine.” Cheryl started to tear up again. “I…”
“Oh, Cheryl. It’s okay. I’ll do it. I’ll do it for you.” I gave her a gentle smile. “I love you.”
“I love you, too.”
With the imminent date arriving, Cheryl and I went to the store Lori “suggested” to purchase the outfit. Neither she nor I was comfortable renting since we had no idea who would have worn it before me regardless of how high end this place was. Cheryl had called ahead and told them what we needed and what sized I was.
“Hi, there. Welcome to D-va’s Designs.” The girl behind the counter greeted us as we walked in. She spoke with a European accent. “I’m Elizabeth. How can I help you?”
“I called last week for a maid’s costume. I have the reference number: M69-4-28.” Cheryl responded. “I got a call saying it was ready.”
“Yes, we received it the day before yesterday.” Elizabeth moved from behind the counter. The dark haired girl was maybe 5 feet in height, very Rubenesque with huge breasts. Her body seemed to be more firm than fat. “I’ll get it for you if you would please wait.”
It was a couple of minutes before she returned. “Here it is! Beautiful isn’t it?”
My eyes popped. It may have been just a maid’s outfit but it was gorgeous.
“I think we might have got the measurement incorrect.” Elizabeth said concerned. “I don’t think this will fit you correctly.”
We realized she was talking to Cheryl. Cheryl cracked a smile. “No, it’s for him. Can he try it on?”
“Of course.” Recovering quickly from her surprise, Elizabeth led me to a change area. It was a nice sized, carpeted area with a couch and a pedestal in front of a triangle of mirrors.
I removed my clothes while Cheryl chatted with Elizabeth.
“I hear an accent. Where are you from?” Cheryl enquired.
“From Poland. Warsaw area, just outside of the capital.” Elizabeth answered. “And you? You have an accent also.”
“Yes, Manchester, England.” Cheryl giggled.
Meanwhile I had hooked the garter belt around my hips to hold up my fishnets and then pulled the frilly panties over them. The dress was a slight scoop-cut front and low-cut back. The hem was short enough to reveal the clips from my stockings. The shoes were black pumps with five inch heels. I had to call out to Cheryl to help with the back zip and hook. They both came into the room.
“Oh Sunshine, the fit is just about perfect.” Cheryl smiled as she did me up. “Step on that stand in front of the mirrors and take a look. You look so pretty.”
I did as asked and took a couple of turns.
“He walks very good in those heels.” Elizabeth commented.
“Yes, he has had practice.” Cheryl revealed. “Lots of practice.”
As I stood facing both Cheryl and Elizabeth, the look of disappointment crossed their faces. I did not understand.
“I have just the thing!” Elizabeth announced and left. She returned a few minutes later with a number of things in her arms. The first thing she held out to me was a black well-padded bra for males.
Cheryl helped me on with it. When the dress was zipped up and covering everything, you really couldn’t tell my breasts weren’t real. I now had sizeable bosoms to compete against Cheryl’s and Elizabeth’s.
Next was a black wig made from real hair, according to Elizabeth. The short bob style curled in around and tickled my neck as it framed my face giving me a very feminine appearance. The little maid’s tiara finished off the look.
“You look so sexy!” Commented Cheryl. “Wow, I think if you had your face done, it would be hard to tell you weren’t a girl.”
I was hard inside my panties and gushed at the compliment.
Elizabeth nodded an enthusiastic agreement. “You could come clean my place anytime you wish!”
“Hmmm… Maybe we should start contracting you out, Sunshine.” I couldn’t tell if Cheryl was teasing me. “I’m sure we could make it work.”
Rather than change back into my regular street clothes, Cheryl let me remain dressed in costume as we drove home. Her hand teased me under my hem. We just managed to get through the front door before Cheryl literally raped me.
Finally the day of my penance had arrived. I was anxious. So was Cheryl and from the email Cheryl received the night before, so was Lori.
It was an all-day thing so I needed to get up and get ready early. I thoroughly showered and carefully shaved the non-existent hair on my face and body. Cheryl allowed me to share her perfumed bath powder. It made my skin so silky smooth.
Cheryl always had such nice surprises for me. Today especially since I had to pay up for the loss of her bet. She held out a wrapped box and handed it to me. With excited surprise I took it from her and ripped off the pink tissue. I didn’t recognized the name on the top but when I took the lid off and moved more tissue, I found myself lifting up a waspie waist cincher. It was black with black roses embroidered through it. The front was hook and eye but had lacing up the back.
After I did up the front, Cheryl helped lace up the back very tightly. The metal stays were stiff as my cock and shaped in my tummy while making my hips flair out slightly. With my constant practice, I was able to do up my own bra but needed a little help with my panties since bending over was difficult. In the future, I would have to remember to put the belly cincher on afterwards.
Cheryl also had to help me with my stockings and garters. As she fished the straps through my panty leg holes, she noted the unsightly bulge. Cheryl pulled the waist of my panties down enough to expose my erection. With what has become normal practice, Cheryl placed the tip of her middle finger against the pad of her thumb and gave me a hard, stinging flick. The cause of that unsightly bulge instantly disappeared and I was able to put on and lock my cock restraining device. And according to Cheryl. “Just in case Lori gets any idea.”
I finished putting on the dress, slipped on the sexy stilettos and donned my beautiful wig with the tiara. I looked so sexy if I wasn’t me, I wouldn’t believe it.
“Sit!” Cheryl ordered, I obeyed.
She pinned my hair out of the way. She plucked and shaped my eyebrows which was pretty painful. She started to apply some foundation first then finished with a little cheek rouge. Next she glued on some long eye lashes and thickened them with mascara which made it look like I was seeing through jail bars. Then with the shadow and liner, my eyes really popped. The ruby red lipstick was the piece de resistance.
“God! If we weren’t in a hurry, I’d fuck you to death!” Cheryl tearfully exclaimed. “You look so hot; so sexy; so… God I want you now!”
The restraining device did its job very effectively. I could feel my surging blood rush to my groin, but was unable to attend any semblance of an erection.
Cheryl drove us to Lori’s. It was a pretty sizeable abode and cleaning it would take the majority of the day for sure. The long private driveway was hidden by a grove of tall shrubbery that surrounded the manor.
“Cheryl. How can Lori afford to have a place like this?” I asked.
“Old money. Her dad is pretty wealthy and bought it for her along with everything else on the condition she also maintained a job.” Cheryl explained. “That’s why we’re at the same company. Her father is the chair of the board.”
I swung my legs out from the car as Cheryl taught me and avoided any unladylike panty exposure. We walked up to the door and rang the bell. We waited a minute before we heard the lock unlatch and the door open. Both Cheryl and I were taken aback. Answering the door was Paul. He was also dressed in a maid outfit; not as pretty as mine but similar. It was a short as mine was to easily show he was wearing garters to hold up his stockings. Again, disappointingly Paul wore low heeled Mary Janes.
Paul invited us inside. The hallway was grand with a spiral staircase a la Tara from ‘Gone with the Wind’. At the top waiting was Lori. She called down in a slight condescending tone. “Hello! So glad you could make it.”
“Hello, Lori.” Cheryl responded in a deadpan voice. “We’re here as per our agreed bet.”
By then Lori descended and was smirking at us face to face. Then she took a good look at me. Her mouth literally dropped open. “Is this…?”
“Yes.” Cheryl acknowledged, not letting Lori finish her sentence.
“Wow! I really didn’t recognize you. You look incredible!” Lori said gob-smacked. “Paul will show you where everything is and will instruct you on what to do.”
I was unsure of protocol and curtsied. I turned to Cheryl and gave her a reassuring “I love you” glance before I followed Paul, but not before hearing Lori tell Cheryl. “Okay. You can leave now. I’ll make sure he gets home safe and sound.”
“I can’t just leave him here!” Cheryl started to protest.
“Titch! The bet was for him. Not for you.” Lori ushered Cheryl out and closed the door.